Oxalyl chloride → HCID 19870597, compound

HRID 330209Notes

Reaction equation

HRID 330209 reaction equation
C(Cl)(=O)C([Cl:4])=O.[C:7]([CH:10]([CH3:37])[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])(O)=[O:8]>C(Cl)Cl>[Cl:4][C:7]([CH:10]([CH3:37])[CH2:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][CH2:22][CH3:23])[CH:16]=[C:15]2[CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=1[O:35][CH3:36])=[O:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 19870567HCID 19870567, compound

Product 1

HCID 19870597HCID 19870597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.88 g) was added dropwise to a stirred solution of methyl 4-[5-(2-carboxypro- pyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (4.2 g) (prepared as described in Example 67, part c) in methylene chloride (100 ml) under a nitrogen atmosphere. After 2 hr the solvent was evaporated, the residue dissolved in ethyl acetate (50 ml) and the solvent evaporated. The residue was dissolved in tetrahydrofuran (50 ml) and the solvent again evaporated, and the residue used directly in the next step without characterization.

Workup

  1. customAfter 2 hr the solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  5. customthe solvent again evaporated

Sources & evidence

ORD record
ord-f4f6a094f9a3489c832e2b289ef5cae1
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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